I used analog pedals starting back in the 1960's, a Fuzz Face and a Vox wah into a Marshall stack ala Jimi Hendrix. There was no such thing as digital anything back then. Then came solid state amps that sounded crappy compared to tubes, until much later generations. One of the big snafus back then is that bands like The Beatles and Creedence Clearwater Revival, using Vox and Kustom amps respectively, helped sell tons of those amps in the USA, but ours didn't sound like theirs, because they were using tube amps, and all of the ones sold in the USA were solid state! Talk about some hacked off people, including me with some Kustoms. That made us all bone up on electronics. When digital came along, we all saw the benefits of it, but good God it sounded terrible at first. Think about how the sound is manipulated through these devices. A digital device uses converters to change your guitar signal into a binary bit-code that goes through software that further manipulates it to add or subtract coded effects, eq, volume, etc, then spits it out through another converter that tries to emulate the analog signal that you sent to it in the first place. A true analog signal path never changes the basic nature of the signal, leaving it analog, but does manipulate it through transistors, diodes, capacitors and other goodies, things normally found in a tube amp anyway.
Having said that, I have used digital multi-effects processors like the Line 6 Studio Pro rack mount through a good tube amp with great success. That tube amp makes all the difference. Plus, with a good amp you can choose to run the pedal board either as guitar > board > amp, or run your guitar straight into the amp, then run the board through the effects loop of the amp. I prefer that way because then your preamp is not effected by the digital signal from the board, and after your signal goes through the board in the loop, it is then tempered by the tubes in the power amp. With a Mark V you could do that and still use your channel switching. But I have done both, depending on the setup I needed. There is no denying that the convenience of having everything in one pedalboard, especially being able to use preset banks to switch from, say, a dry clean rhythm sound to a screaming solo sound with chorus, echo and reverb with a single button, is fantastic. Remember our premise for versatility? There is no way you could turn on and off all the individual pedals you'd have to, to get the same sound during the one-beat space of time you have to go from playing rhythm to solo and back again. Oh, and changing your volume somehow, all especially difficult if you are singing at the same time.
Needless to say, analog pedals will give you the "truest" sound if you use pedals that have a true bypass (meaning when the pedal is off, it doesn't effect your sound in any way. A lot of pedals do, and even true-bypass pedals will change it because you have introduced another "thing" into the line, adding capacitance.) One of the big advantages to using individual pedals is that you can change them out without breaking the bank. I've done this a lot, too.
Digital pedalboard development (the big leap was using 32 bit floating processing) has progressed now to the point that even many guitar players would find it difficult to tell the difference from analog in a blind test. For decades I've played in some of the biggest name bands in my region, and I've used both types of setups. Personally, yeah, the analog stuff sounds better, but realistically, especially with the current level of technology, not a single person in any audience you play for will know the difference. Audiences listen to the singer, not the guitar player. So the bottom line is, who do you want to please? The answer has to be, yourself. If you are not getting the sounds you like, you are not going to play as well as you can. But also, if you are stumbling around on stage trying to stomp a bunch of pedals when you could have hit 1 pre-programmed switch, you won't be happy. You CAN get digital to sound good, and analogue pedals can do it too. As you said yourself, only you can decide.
One quick story at the risk of boring you to death (did I already do that? Sorry!) One night my band Druid was the opening act to be followed by Cactus and Bob Seger in a 7,000 seat, packed auditorium. Cactus missed their flight and called in to cancel right when we were ending our set. In the middle of a song, the producer motioned me over to the side of the stage, behind the curtain, and told me "Cactus isn't coming, you need to play another hour." The problem was, we were out of songs we prepared for that night! We decided to start jamming like we did in my band practice bedroom, and went into individual solos. I started mine. I was using a Les Paul with the Fuzz Face/Vox wah setup straight into a 100 Marshall 8x12 stack (this was the early 70's) cranked wide open on both channels. About half-way in, I was overcome with this fabulous feeling because my sound was just incredible. Notes were just melting off the fretboard, sustaining forever, like they were alive, and hearing it all with the natural echo off the walls of this huge auditorium just pushed me into another level . The room, the stage, the people, just disappeared, and I started playing as though I were at home sitting on the floor in my pajamas with nobody listening but me and God. You know how when you are really into it you just disappear into your own head? That's what happened, because of the sound. After one little passage the crowd started spontaneously clapping, and realizing I was connecting with them, which pushed everything a notch higher. "Floating on clouds" is just an expression, but I've been there, it can happen. I really don't remember what I played, but suddenly came out of this daze and realized I'd been playing a really long time! I felt embarrassed and quickly ended it, but the crowd applauded enthusiastically, so I guess it was okay. The point here is, sometimes magic happens, and if you set it up right, it will happen to you.
Enjoy, and May Your Decisions be Wise!
Scrench